


It Be the "C"

by Alpha_Writes



Category: Supernatural
Genre: Alternate Universe - Pirate, Angst, Death, Internal Conflict, Language, Mild Gore, POV Castiel, angels as the royal army, because this time they really are sailors, hunters and demons as pirates, kinda salty Cas, mention of rape
Language: English
Status: In-Progress
Published: 2018-06-14
Updated: 2018-09-10
Packaged: 2019-05-23 12:03:12
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 11,231
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14933910
Author URL: https://archiveofourown.org/users/Alpha_Writes/pseuds/Alpha_Writes
Summary: Lieutenant Novak at first was bewildered at the order to save the dreaded Captain Winchester from the rotten Demons. However, the soldier didn't know that retrieving this pirate would be a lot harder than first thought.





	1. Wanted Dead or Alive, Preferably Alive

            Lieutenant Novak quickened his pace. He could have no error today. He committed too many over this past month. From failing to capture the pirates known as “ _Lucifer’s Demons_ ” to speaking out of turn towards the Commander. He was in deep, deep water. However, not as deep as the drowning pirate in the sea. Speaking of which. The Lieutenant signaled to his men to start surrounding the Demons. From what his Commander told him, Captain Winchester of the Black Impala, the man at the bottom of the sea, was captured by some of “ _Lucifer’s Demons_ ” and he was sent to retrieve him. On why a filthy pirate was of interest to the crown he didn’t know. He didn’t ask either. He was given an order therefore he must follow it.

            Perhaps, this was finally an opportunity to rid of the fowl Capitan Winchester. All Jimmy knew was that if he didn’t bring back the pirate alive, _he_ would be the one at the bottom of the sea.

            He watched as the other pirates on the dock laughed at the drowning man struggling to break free of his ties. Giving the signal, Jimmy and his men rushed the pirates. The small, but skilled, army took out the Demons easily. They may be the largest pirate crew but their skills were certainly lacking. How one of the most feared pirate captains in all the Caribbean was captured by them was beyond him. Novak raised the drowning pirate from his watery grave and into the light. While his men were scanning the area he checked if the pirate was still alive.

            The pirate himself seemed very clean and… not as putrid as most of his kind Jimmy encountered. He’d been stripped of most of his clothing and was left in only a pair of black britches. The Lieutenant spotted a tattoo on the pirate’s chest. It was of what looked like a pentagram, surrounded in flames. He found no pulse so started to do chest compressions. He wasn’t entirely sure what it did but the doctor said to do it if someone wasn’t breathing and had no pulse.

            While doing this, he scanned the pirate more. His sun-kissed skin was dotted by freckles all over his nose and shoulders. His short dirty-blond hair was flattened by the salty water, and covered his forehead. One gold ring hung from his left ear. Jimmy didn’t know if he had any weapons with him, yet, the pirate captain had his wrists and ankles bound so there was nothing to worry about.

            Then, the man beneath him started to cough up water and a bit of blood. His eyes opened to reveal the greenest green. The green orbs turned from confusion to anger in a half a moment. That anger was directed at Jimmy.

            “Let me go you filthy Angel!” Captain Winchester seethed, his voice hoarse. He wriggled from Jimmy’s grasp. This was surprising because hadn’t he just been drowning moments before? Caught off guard Novak jumped back, letting the pirate worm away to a log that had clothing draped over it. Gaining his wits back, he scrambled up to his feet and tried to grab the outlaw. By then the man in ties was no longer bound and had cut himself free with a lone sword on the ground. Because of this, the Winchester was up on his feet. Well, as much as he could be. He must still be effected from almost dying. Even with this fact, before Jimmy could unsheathe his blade, the pirate had tackled him to the ground. He grunted as he slammed into the wet sand. The last thing he saw was a fist headed to his face, then darkness.

            Once the Lieutenant woke, he was greeted by the concerned and frustrated faces of his troop. Slowly, but surely, he picked his head up and cringed into a sitting position. A massive headache rung in his skull. He looked to his men.

            “What happened,” he croaked.

            “We killed the Demons. However, the Hunter got away,” one reported, grimly looking down. He pitied the solider. Jimmy placed a dirt-covered hand on the privet’s shoulder.

            “Do not hang your head, solider, I am just glad there were no Angel casualties.” He gave a forced smile and asked to be helped up. Demons. Hunters. Angels. All short-hand terms for the men at war in the Caribbean. Demons, were the nastiest of the bunch. They will stop at nothing to destroy every town along the seven sea’s shores. They are known to murder, pillage, rape, and deface men, women, and children. Jimmy believed in no _true_ evil. But the Demons got real close. Commanded by Captain Lucifer, they were hell bent on taking over the whole Caribbean. And Captain Lucifer, even thinking about his name would send shivers down your spine. He is the most dreaded pirate alive. Lucifer the Savage, people call him.

            The second most dreaded is the pirate that just escaped. Captain Winchester, commander of the “ _Demon Hunters_ ”. They used that name to cause a spark with the Demons. The groups are sworn enemies. The Hunters tend to be much nicer to the people of the land and sea. They are very efficient in their ways and savvy in others. Yet, they don’t take to kindly of people who don’t share their ideals. The Hunters would’ve been great allies to the crown if his battalion wasn’t also on that list.

            All pirates, and frankly everyone, calls the royal army “ _The Angels of the Lord_ ”. There is differences in the definition of it between folks. The people who live under the Lord use the name in good health, a word of hope in a world of uncertainty. The pirates however, use it ironically and as an insult. As if being a saint is somehow undesirable. But, alas, this is how things are.

            Jimmy would not dare to be pirate-less in the eyes of his Commander. So, he dismissed his troop to their quarters as he went on. It is to be noted that the path he was about to take would be terribly dangerous, and incredibly stupid. This is why he dismissed his soldiers. They have families to return to. Mothers, fathers, wives, sons, and daughters. Novak on the other hand, had no family. Mother and father died of old age, and his wife and child were taken from him by the sea orcs. His darling Amelia and his precious Claire. In turn his hatred for the bastards burns as the sun does. He was tempted to find the pirate only to kill him. Go back to Commander Uriel a hero. But all the same, he asked for a rotten, good for nothing pirate still breathing so he would deliver. First, he needed a disguise. Where he was going, you didn’t want to be an angel

* * *

 

            Adjusting his blade under his tan coat the soldier walked into the alehouse. The place reeked of alcohol and lust. Call women lined the street of the esteemed _Harvelle’s Roadhouse_. Jimmy had heard of many great things from the brewery. He wasn’t much of a drinker so he had never tasted the owner’s beers and ales. The owner, Ellen Harvelle, was accepting of all in her establishment. All except Demons of course. The thing was that her customers weren’t as accepting as she is. It he showed up, clothed in army colors, he’d be dead before he stepped foot inside. So, he donned on regular clothes for this occasion. Novak had never been to the alehouse and was glad he hadn’t. Multiple pairs of eyes landed on him as he entered. He wasn’t there for making friends however. He was there for answers, so he trudged on.

            He sat at the bar waiting to be served. A woman, maybe early forties, spoke up cleaning a glass.

            “Howdy stranger. What can I get ya?” she greeted, a welcoming smile on her face.

            “I need to talk to the owner of this establishment. Ellen Harvelle,” he stated, slightly lowering his voice in fear of eavesdroppers.

            “Who’s askin’?” she asked, suspicious. Jimmy sighed and leaned in over the bar.

            “Please, it’s urgent. I’m looking for someone,” he pleaded. The woman looked at him for a moment, eyes squinted.

            “You aint tryin’ to kill anyone now, are ya?” she questioned. Her voice turned cold for a moment. The sound made his hairs stand on end.

            “No… no ma’am. I’m just trying to find someone is all,” he stammered slightly.

            “So you said. Well, it’s nice to meet your acquaintance. What can I do for ya then?” she said simply. The tension easily slipped away and he relaxed.

            “You are Mrs. Harvelle then?” She nodded. “Well, I’m looking for Captain Winchester. I have reason to believe he would go through here to get supplies,” Jimmy whispered. She on the other hand, laughed. Quite loudly. Which drew some odd glances.

            “Don’t lie to me, boy. You _are_ tryin’ to kill someone. The only people who wanna know where that bastard is, are assassins, Demons, an’ Angels,” she chuckled. He felt his neck turn red.

            “I assure you that is not what I intend to do. Trust me, if I was going to kill him I would’ve already done so,” he argued. This only made her laugh more.

            “Cocky are we?” He put his head in his hands.

            “He is a person of interest. I only need him for help and that is all I can tell you,” he mumbled. He was slightly disgusted at the words that escaped his mouth. Asking a wretched pirate for help. Just brilliant.

            “I’m just pullin’ your leg, lad. I don’t normally send strangers to their deaths but since you are so diligent. _Ash! Get out here!_ ” she yelled to the kitchen. Seconds later a drunken man stumbled from the doors. The man had long brown hair and a worn shirt with ripped sleeves. A single silver ring pierced his left ear.

            “Yep,” Ash stated simply.

            “Show this man to the son of a bitch himself.” She gestured the two men out of the building. Jimmy gave her a short thanks and farewell before Ash dragged him out of the alehouse. He just hoped things didn’t end as they did last time.

* * *

 

            They walked for what felt like days. By sometime around midnight, the still drunken bartender and anxious Lieutenant arrived at an abandoned warehouse. Ash bid Jimmy a farewell before wobbling back towards the alehouse. He hardly thought that was safe but decided to say nothing. He had bigger things to deal with. First, he sized up the building. It was small and out in the middle of nowhere. Perfect for squatting down to hide. Drawing his blade he took caution waking in. This time, he would not underestimate the pirate. However that wasn’t enough as when he foolishly walked in the front door, he triggered the booby-traps. Sparks flew as small bombs went off. Gunpowder clogged his nose, explosions made him deaf, and the sparks made him blind. Things were already not going well. Blindly he ran through the warehouse and slowly his ears caught up with him. Then in an instant, he was fighting. With whom he didn’t know. He was just clacking swords with an unknown opponent. He couldn’t see but he could still hear his attacker shuffling in the dirt. From what he could tell, the other was very savvy and almost got him a few times. However, they were evenly matched. Granted, Jimmy’s sight was still absent so he felt he could’ve taken the intuitive if that weren’t a truth. Setting aside the fact that it was probably pitch black for both of them in the dark night. But that is beside the point.

            The dark spots in his vision were starting to wane, but his adrenaline was just kicking in. Now he was able to pick up the pace, placing his footsteps in more precise spots. Ever since he was a young boy, Jimmy loved sword play. It was more than self-defense, more than a way to survive. It was art. Dancing with your opponent, each swing, each movement a calculated step in achieving victory. And, surprise, surprise, pirates had to take something beautiful and tactful, and destroy it.

            Just as Novak gained the upper hand, Captain Winchester pointed a gun at his head.

           “You cheated,” Jimmy gasped.

           “Pirate,” he taunted, giving a satisfied smirk. Pushing Novak back, the pirate kept a firm grip on his pistol. “Who are you?” he demanded. Might as well play nicely now. There was nothing else to do. Dropping his sword he put his hands up in defense.

           “I am Lieutenant Novak of the Garrison. An Angel of the Lord,” he answered.

           “I figured that much. I mean what do you want?” he spat.

           “Well, I’m the one who gripped you tight and raised you from perdition,” Jimmy began.

           “Thanks for that,” Winchester sneered. “Why would a Lieutenant save me? What do the Angels want with me?” he questioned, moving closer to Jimmy. Backing up into a wall, he did his best to suppress his fear. Swallowing, he told what he believed to be the truth.

           “We have work for you.”

**Notes for the Chapter:**

> Hello Readers! I know, I know. Terrible tittle, but I just couldn't stop thinking about the joke Jared and Jensen made at a con once so here we are. I'm a big slut for this AU and I got this idea from a post on Tumblr. Samkatdiz did an amazing [fanart](https://78.media.tumblr.com/3b20b87eea3f192bb31d0201b55e5f2c/tumblr_moj0igVhhl1ryclkro1_1280.png) that I took a lot of inspiration from for the last scene. Anyway, hope you enjoyed! Till you read again.
> 
> -Alph <3


	2. How to Turn Your Public Argument into Performance Art

**Summary for the Chapter:**

> Traveling with a pirate turns out to become the number one thing on Jimmy's "Things I Hate" list. And trust me, it's extensive.

“What kind of work?” Captain Winchester asked, steel in his voice. Novak could already tell this was going to end very badly for him. Maybe if he told the truth and nothing but, the pirate might spare him. Each moment he didn’t speak the mad man became more and more furious. “Well? I don’t have all night, chuckles,” he spat.

            “I don’t know,” Jimmy said, firmly.

            “Ya don’t know. Well I think that answers this question. Did you just come over here to bug me? These prank things are gettin’ real-,”

            “I heard there was money involved,” he cut him off. Now, this may or may not be a lie. He was sure his Commander wouldn’t enlist the help of a psychopathic murderer without having anything for the pirate to have in return. This seemed to have caught his attention. The pirate looked at the Angel with what people call a shit-eating grin. Slowly, the Hunter lowered his gun and sheathed his sword, not breaking eye contact with Jimmy.

            “I’m listening.”

* * *

 

            With some convincing, the pirate beckoned the soldier to the alehouse he previously visited. This time instead of only eyes on him, the pair was greeted by a large cheer when they walked in. Some people said things like “The Captain himself!” and “You son of a bitch! You’re still alive.” The pirate captain would reply with things like “Heya, cunts!” and “Of course I am, ya bastard!” Charming. The boys had to fend off call women and ladies alike to get to the bar. Jimmy compared and contrasted his first visit to his second with the pirate. He knew he was famous but not like this. The Lieutenant thought he was _infamous_ instead of… whatever _this_ is. He was learning many things that night. And that was only the beginning of it.

            They got to the alehouse in a much shorter time period than it took to walk to the warehouse. This was because of a short cut Ash forgot to mention. He was probably too drunk to know his way.

            “Thought you were gonna kill ‘em, Dean,” said a familiar voice.

            “Change of plans. I may get a few coins outta this,” the Hunter responded to Mrs. Harvelle. He tapped the bar twice and showed a two with his fingers. She served him two beers and whispered in his ear. What she whispered he couldn’t hear and before he could ask she disappeared to the other side of the bar.

            “What do you mean by ‘change of plans’?” Novak asked. The pirate passed him a beer.

            “Ah, I may have asked Ellen to send you over to warehouse if you went after me. I was gonna kill ya but that aint what happed. Now did it?” The man took a long chug of his beer before continuing. “So, what’s this I hear about money?”

            “Well…,” he stalled. He now really wishes he asked more about what they were going to do to him. Jimmy didn’t want to lie to him. Mostly because his buddies would probably want to go after him. It also felt wrong to lie for him so he rarely ever did. “I don’t know the details, but if you would just come with me I would take you to my Commander and then-,”

            “Woah, woah, woah,” the pirate stopped him. “I haven’t seen my little brother in months. I aint goin nowhere with your feathery ass till’ I see my crew again and let ‘em know I’m alive,” he argued. The sentence held a lot more emotion that the pirate intended, he thought. Knowing about his brother made Jimmy feel slightly selfish. The soldier sighed.

            “Fine, how long will this take?” he gave in.

            “A couple a’ days,” he responded, taking another, long, chug.

            “A couple of days?” Jimmy exclaimed. He didn’t have that long. He should have had the pirate behind bars yesterday. He ran out of time as it is. No way was he going to get back in a couple of days without everyone thinking he was dead or worse. “I don’t have a couple of days. I need to get you and me back to my Commander, _now_ ,” he demanded. The Hunter slammed down his beer with a burp. Putting his wrists out, he faced Jimmy.

            “Okay. Take me away soldier,” he said, a smug look on his face. Novak looked to his out-stretched arms then looked to the pirate, then to his arms, then back again.

            “You are being oddly compliant. Why?” he asked, slightly pulling back. Putting his arms down the pirate captain went back to his almost finished beer.

            “Because, if you even look at me wrong, everyone in here will make sure you’re dead before you hit the ground,” he said, gesturing to the tables around him. Something the soldier hadn’t noticed before is every able man was eyeing him, up and down. This was not good. Not at all. Now his only option was to go on a wild adventure with a blood thirsty pirate. Lucky him. Things were moving too fast. All he wanted was to fulfill his mission, not be threatened with death.

            “Fine,” Jimmy growled.

            “Great!” He looked down to his untouched bottle. “You gonna drink that?” asked the pirate.

            “I don’t drink.”

            “Bummer.” Downing the rest of his beer, he beckoned the soldier to follow him. Whatever Jimmy had just gotten himself into, he was going to regret it.

* * *

 

            The pair silently trudged through the thick brush. They had been traveling for hours in the swamps and Jimmy was starting to really hate bugs. In the morning sun, beads of sweat laced his forehead and streamed down on occasion. The humidity was suffocating, the Lieutenant had to raise his head above the cloud of humidity just to breathe. However, the heat wasn’t the only thing constricting his throat. The two haven’t traded a word since the alehouse. The silence of buzzing bugs and whining frogs was unbearable. Jimmy decided to speak up.

            “So your first name is Dean, is it?” he asked. The man in front of him huffed.

            “Where’d you hear that?” Novak evaded a pile of droppings.

            “I, uh, I heard Mrs. Harvelle say it,” he explained, wiping his forehead of sweat.

            “Well it’s only polite for you to introduce yourself now, is it?” the pirate mocked him. The soldier strained a laugh.

            “I did,” he said through gritted teeth.

            “Ah yes,” he recalled. “Lieutenant Novak of the jackasses.”

            “You don’t have to be rude, pirate,” he shot back.

            “You say that like it’s an insult.” Dean pushed away a large branch.

            “It is an-.” The branch swung back to whack him in the face. The swashbuckler laughed as he walked away. Jimmy broke the branch in frustration and ran after the pirate. “At least I have an esteemed job to do instead of running around and, and just killing people because I can. I serve a cause, what do you stand for? Stealing and violence?” he hissed. Dean stopped and turned back to look at him.

            “The difference between us, birdbrain, is I kill people who fucking deserve it. You kill people who you are told to kill, like a good little bitch. Who’s fighting an esteemed cause again?” he countered.

            “Who gave _you_ the job of judge, jury, and executioner? All you pirates are the same. Hating the royal army just because we hold you to some ideals you may not like. Because you don’t like rules. Because you think you are _above_ the law,” Jimmy debated, grabbing the handle of his blade. Dean scoffed.

            “You Angels think you’re _so_ entitled. What? Did God give you your jobs? _No._ You were born into them. You have zero clue as to what _shit_ us lower class has to deal with. I’ve had to fight for my life time, and time again. So _don’t_ get me started on the _‘rules’_ ,” Dean argued, yelling in his face now. Jimmy has had enough of this nut-job. He was now sure his Commander surely wouldn’t mind if such an annoying little speck was eliminated. This bastard had absolutely no idea the hardships he went through to become Lieutenant of his troop. He’s lost his only loves to his kind and now he has to hear the lecture of one? About how hard it is for _him_? He tightened his grip on his sword.

            **_Bam! Bam!_** The first shot made Jimmy duck into the shrubs. The second, spewed splinters from the tree next to them. Dean ducked as well and pulled out his own pistol. Jimmy unsheathed his sword. He heard that you should never bring a sword to a gun fight. However, it was his only weapon and he wasn’t going to lay his life in the hands of a pirate. The two rested their backs on a log to shield themselves from the shots. No other shots were fired but they weren’t going to test their luck.

            “Whoever is on my property better get the fuck off before I blast ya to hell,” a ruff voice warned just behind them. Then, the pirate laughed. He _laughed_. He was as insane as he has heard.

            “Man, Bobby. Is this how you welcome home someone who’s just come _back_ from hell?” he shouted back. The crunching of leaves and squishing of mud came closer to the two and Jimmy’s heart raced faster. An older man came out behind the log. His head was clothed in a red bandanna, and wore a worn brown shirt with black slacks and weathered boots. A large silver ring hung from his left ear, that made his head look slightly smaller. An astonished look stained the old man’s face as he saw the two boys crouched down.

            “Dean? Is that you?” He said, perplexed.

            “Heya, Bobby. It’s good to see ya.” The two shared an embrace as Jimmy shakily got up.

            “God, boy. I thought I’d never see ya again. How… how did ya…,” the man gushed as he put a hand on Dean’s dirty face. Bobby’s eyes caught Novak’s. Gently pushing Dean aside he pointed his gun to Jimmy. “Who’s he?”

            “Well, he’s the one who… helped me get away. This is Lieu-.”

            “Jimmy. Jimmy Novak,” he cut Dean off.

            “Well, ya did somethin’ real kind, Jim. We’re in your debt,” Bobby said, nodding to him. The old man’s response was very genuine. It caught Jimmy off guard. The fact that someone could care so much about a pirate was beyond him. But, it was obvious of the history the two had. He almost became… guilty. Jealous.

            “It was really nothing. No need to thank me,” he assured. Dean rolled his eyes.

            “Yeah. And he’s also-.”

            “Just someone trying to help,” Jimmy cut in again, this time more firmly. He really didn’t want his cover to be blown. Not with a man who had a gun and wasn’t afraid to use it. Then again, he seemed to be on his good side. However, he didn’t want to risk it. A lot of outsiders didn’t like the Angels and the government in general. Dean sighed and seemed to drop it.

            “Well, Jimmy, you’re welcome in my humble abode. You two must be hungry. Musta been in the sun for hours. Follow me for some shade and food,” he offered, walking in the opposite direction. Jimmy gladly accepted and followed the man. This was not without a jab in the ribs by the pirate. He was tempted to jab back but decided not to be tempted by his childish games. Things might just be looking up on this adventure.

* * *

 

            The old man and pirate captain caught up as Jimmy held a beer he wasn’t going to drink. He sat awkwardly in a chair as Bobby confessed how much he missed the Hunter. Looking around in the small cabin he spotted things like paintings of a man and woman. The cabin itself was very homey and lived-in. Decorated with many souvenirs of past adventures it seemed. Jimmy longed for something like this. His quarters back in the castle were less than satisfactory and were much like a hole in the wall. Catching himself daydreaming he turned back to the conversation. They must have talked for hours before Dean mentioned a man named Sam. As they talked more he found out that Sam was Dean’s little brother who, in his absence, had been running The Black Impala and its operations.

            “That boy is goin’ to be ecstatic to see ya, Dean.” Bobby smiled warmly.

            “I can’t wait to see ‘em. You know when he’s gonna come here for supplies?” Dean asked, taking a swig of his beer. The soldier guessed it was true that all pirates were alcoholics. He stopped drinking because it only made him think more. And he didn’t want to think.

            “Tomorrow, I’m sure. Our schedule got mixed up cause those fuckin’ Angels found one of our trade routes and bombed the thing. Made things a whole hell of a lot harder,” he grumbled. Jimmy slightly sank in his seat. He knew exactly what he was talking about. That trade route was a major victory for the Angels. They became one step closer to ridding the world of filthy pirates. Guilt twisted at his stomach. But why was _he_ guilty? They brought this on themselves. If they would just follow the rules instead of being so greedy they wouldn’t have to worry about trade routes.

            “Huh, really?” Dean side-eyed Jimmy. He pretended not to notice. “Alrighty then, I’ll bunk up here then to wait for ‘em.” Taking one more sip he set the beer aside and stood up, popping his back. “I’ma catch some Zs. I haven’t slept for two days,” he yawned walking to the busted up couch.

            “Good idea. Oi, Jim, I’ll grab a pillow and a blanket for you to sleep on the floor. Sorry that I don’t have another couch or something.” Bobby got up and walked to the closet in the hallway.

            “Ah, no. He’s sleepin’ outside,” Dean contented.

            “Excuse _you_. Whose house it this? Sorry boy, Dean’s just an asshole,” Bobby chided. Jimmy silently chuckled and gave the pirate a smug look. In return, Dean gave him the bird before resigning to the couch. He didn’t care, he had won this battle and you know what? It felt good.

**Notes for the Chapter:**

> Hello Readers! I don't know why but I have SO much fun writing argument scenes. They can be just so heated and I love it! This one's kinda short but I realized if I clumped it with the third chapter it would be WAY too long. So have this while I finish the third chapter. Anyway, hope you enjoyed! Till you read again.
> 
>  
> 
> -Alph <3


	3. The Fine Art of Bullshit

**Summary for the Chapter:**

> Maybe, just maybe, Jimmy might be wrong.

            Jimmy slept till sun rise of next morning. He didn’t realize how tired he was. Thinking back to it, he had been awake for almost two days straight and done a lot of walking within those days. He awoke to a kick in the ribs. Snapping his eyes open he sat up and saw the Winchester standing over him.

            “Wake up. Breakfast. Get it while it’s still here,” he said, stones hardening his voice. Novak groaned and gave him a dirty look. Dean ignored him and walked to the dining table. Rubbing his side, he slowly got up to his feet. Smelling cooked eggs and ham Jimmy’s stomach growled like a dog. He also just realized how hungry he was. Before going to sit with the two men at the table, he checked his clothes to see if anything was stolen or added that might be a problem later. Finding nothing, he padded his way to the table where a pile of eggs and ham awaited. He thanked Bobby for making the meal and gladly dug in. However, his intake of the food wasn’t nearly as ravenous as the pirate across from him. He could only stare as the man stuffed down his food in a matter of what felt like seconds. When Dean was done with his food, he looked to the soldier with a look that said ‘Yeah, and?’ Sighing, he went back to his own plate and let his thoughts wander.

            He still couldn’t get a grip on what exactly was happening to him. All he set out to do was save a stupid pirate and bring him back to his Commander. Now he met a man who hated his brothers in arms yet had no idea that he was the thing he hated. All on the same token he managed to be on his good side. Jimmy looked to the pirate who was cleaning off his plate with water. What was so special about him? What made him desirable to be around? The old man, Bobby, seemed to have quite a fondness for him. It just didn’t make sense to him. Who would love a blood-thirsty, filthy, no good, dirty, rotten _pirate_? He watched in silence as the old man lectured Dean on how stupid he was for doing something that Jimmy didn’t hear about. Maybe a father would, he thought. But Bobby wasn’t Dean’s father, at least Jimmy hoped. Dean called him by his first name, there needs to be bad blood between a father and son in order for that to happen.

            “Wait… you hear that?” Dean’s voice lifted him from his thoughts. Jimmy heard nothing. “Is that my Baby?” he exclaimed, running outside. Jimmy didn’t know the pirate had lover. Maybe it was true that every half has its other. Following the pirate outside to the beach with Bobby, he asked about this ‘Baby’.

            “Who? Oh, yeah, she’s quite a beauty. I’m quite jealous of her myself,” Bobby said fondly. “We went through a lot, she and I. I’m just glad his pops pasted her on,” he finished. Pasted her on? What kind of a woman what this? Must be some kind of call woman, he theorized. That made since. They were talking about a pirate falling in love. However, his theories would come to a screeching halt when he saw who the ‘Baby’ was, or rather what.

            “A ship?” Jimmy questioned, looking at the giant gaff ketch. The ship was large but small enough to be quick. The black sails were adorned with a red pentagram, similar to the pirate’s tattoo. Finally, putting the pieces together he concluded that Dean’s ‘Baby’ was none other than The Black Impala. Of course, the Angel realized, the only thing that a pirate loves more than killing is his ship. How the man was able to hear his ship from many yards away was the real question. Bobby waved to the crew on the ship as they got closer to the shore. As they docked at the small dock next to the beach, Dean hid in the foliage. Jimmy thought it was strange but didn’t comment on it. A tall man walked off of the ship. The man wore a red shirt with a brown over coat that brushed at his feet. He had long brown hair that went down to his shoulders covered by a tricorne and a small gold ring hung from his right ear. His black boots clacked on the dock as Jimmy and Bobby went to greet him.

            Anxiety clenched at his mind and heart. He didn’t know why he was so anxious. Maybe it was because he was about to meet one of the deadliest pirate’s crew mate. 

            “Mornin’ Captain,” Bobby greeted solemnly. Jimmy felt his hands start to clam. Not only was this a crew member of The Black Impala, but it was the stand in captain. And, using context clues, he thought the man to be Dean’s brother, Sam Winchester. He had nothing to fear, really. As long as his identity was kept secret, he would be fine. However, Jimmy had no clue if a certain pirate would keep his mouth shut.

            “Bobby, I told you to not call me that. Too formal,” Sam chided. The man seemed broken as he said it, a strange melancholy overtook his form. He saw the awkward soldier out of the corner of his eye. “Who’s this?” he asked, curiously.

            “This is Jimmy Novak. And he brings great news,” Bobby answered, grabbing Jimmy by the shoulder.

            “Heya Sammy!” Dean shouts to Sam as he walks over. Surprise and shock stained Sam’s face like wine. As Dean walked up the steps of the dock, his brother stood frozen and pale as he’d seen a ghost. However, as soon as the pirate captain was in arms reach, Sam tackled him with a bone-crushing hug. Dean chuckled at his brother’s enthusiasm. That chuckle was slightly muted by the pain from the hug he was trying to conceal.

            “Am I dreaming?” Jimmy heard him whisper. Sam pulled back, a smile that reached to the moon and back, plastered on his features. “Dean! How’d you get back? I thought for sure you…,” Sam’s voice trailed off.

            “Well, uh, I had _some_ help. But those demons aren’t really a match for me,” Dean boasted. Jimmy frowned. Of course he would take all the glory. But why did he care? Jimmy didn’t fight for the riches. So he could take all the credit if the pirate wished to blow up his own ego. However, in that instant, he wouldn’t stand for it.

            “I was the help,” he cut in. If looks could kill, Jimmy would be slaughtered by the sheer intensity of Dean’s glare. Sam, however, looked at him with much, much kinder eyes. They seemed to melt at his words.

            “Thank you. Really, you- I- you really- you really don’t know- just- thank you,” Sam babbled, stumbling over his words. Jimmy gave a small bow to the pirate. Again and again he has been amazed by the love and compassion this pirate captain got. He even amazed himself at the generosity he gave in return. He could not forget his mission. This meeting was a good thing for now, after he meets his crew, Dean would fulfill his promise and come with him to his Commander. But Jimmy knew a pirate’s word meant nothing. If he had to use force he would. He would have to be sneaky for of the numbers of pirates around him. Speaking of which.

            Jimmy looked to the boat’s edge which was now lined with many other pirates. All whooped and hollered at the sight of their captain. As Jimmy looked closer he saw that there were not only armed men but women as well. It was very unusual that a pirate captain would allow women to man a job on their ship. Perhaps, Jimmy judged too quickly. Or maybe he was holding the women against their will. He would not let his guard down around these filthy pirates. He counted nine at the edge with maybe 20 or so more behind them, milling around. All nine came down to greet their missing captain.

            “You’re alive!” a red-haired woman exclaimed as she gave her own crushing hug to the captain.

            “Course I am, Charlie. I wouldn’t leave y’all,” Dean said soothingly, hugging the woman close. This continued with the rest of the eight pirate whom came off the ship. The softness Dean showed to his crew almost touched Jimmy. Almost. Varying exclamations of surprise and answers were said between the crew and captain. Jimmy felt more out of place than ever.

           Bobby introduced Jimmy to the crew off and on the ship. In celebration of Dean’s return, the Hunters suggested a huge party filled with food, beer, and stories. In the midst of the cheers and happy reunions Jimmy almost forgot his mission. _Almost_.

           “Dean Winchester, do not forget what you need to do,” Jimmy warned as he pulled the captain aside.

           “God, would you get off my ass, bird-for-brains? Let me just be with my crew. In the mornin’ I’ll see about that money you and your leader will offer me, yeah?” Dean shoved off the Angel, leaving him alone in the dreadful sun. He could only watch as the pirates laughed as music rang out in the ship. He watched as Captain Winchester lovingly caressed the ship’s wooden masts. He watched as a whole different world unraveled before him. This world was parallel from his own. It was true, both worlds had a crew, a leader, and… somewhat of a cause. But this world, this one had something Jimmy never had, or thought he wanted. Freedom.

           No, no. They were _not_ free. Just reckless and entitled. Jimmy was free. Free to command his troops. Free to live in peace instead of on the run. Free to walk the land in no fear of being arrested. _They_ were the criminals. He had everything the pirate didn’t. _Loyalty_. _Security_. _Purpose_. So, with that revelation, Jimmy declined the invites to join, and simply watched as the pirates partied into the late hours of the inky night. Their bodies only illuminated by candles and the moon light. He watched the push and pull of the tides on the beach, counting them until he fell into a deep slumber.

* * *

 

            How he woke this morning was, decidedly, much worse than how he woke the morning before. A kick in the side was fine. The throbbing stopped after a while. However, when you are tied to a chair, on a ship, with angry pirates around you, you can’t just wait it out. Fully grasping the situation, Jimmy struggled only to find tight ties and strong ropes. His heart felt like a barrel going downhill, dropping deeper and deeper into his stomach. Now, he was surely to die. Dean had obviously ratted him out and now he was going to die. He had a good run, made many advancements for the good of his Lord. He sighed a lengthy sigh, resigning himself to the white horseman.

            “Well, get on with it,” Jimmy sighed, closing his eyes. Instead of a bright white light, pain erupted in the side of his face. Throbbing, stinging, and hotness consumed his face.

            “You are gonna tell us what the dicks with wings want, Angel,” a female voice spat. This was not going where he intended. Opening his eyes Jimmy saw a woman who was just inches from his face. She had dark eyes, with dark hair to match. Gunpowder and soot covered her fearsome expression. He gulped.

            “I think that’s good enough. Thanks Eileen,” Sam Winchester said to the woman, coming out of the shadows. The woman, Eileen, gave Sam a sweet smile. Giving a ‘no problem’ she simply walked out of the quarter’s doors, not without slapping Sam’s… rear on the way out. This action made him slightly jump. Now, Jimmy was completely confused. He woke up on a swaying ship, been punched in the face, and witnessed… whatever that was in the first few seconds of consciousness. ‘Bad day’ couldn’t even cover the context.

            “What was _that_ for?” he said, stunned. A Dean Winchester also came from the shadows of the poorly lit room.

            “Intimidation,” he stated, bored.

            “Intimidation?” Jimmy questioned.

            “Well, most of it was for intimidation but Miss Leahy has always wanted to punch an Angel so, there’s that,” Dean revealed. Jimmy scoffed. Intimidation? He didn’t think it was because of that at all. The pirates just wanted to use him as target practice. “You intimidated yet?”

            “You broke your promise, Hunter,” he accused, his voice gruff.

            “I didn’t promise jack-shit, cupid. However, I do still want to get paid. However, dos. Ima do it on my own terms. _My_ rules. If I bring you back alive but in pirate chains, they’ll see I’m not putting up with any shit. Got it?” he clarified, emphasizing his point with a blade to Jimmy’s neck.

            “There is truly no need for this childish game,” he struggled from the knife.

            “Childish game? Really? You of all people should know that this is _war_. I’m not going to risk the life of my crew mates for your ‘cause’. _My_ rules. _My_ payment. If my brother and crew are not safe I aint doing anything. Got it now?” Dean pressed the knife, oh so harder on Jimmy’s neck. Jimmy thought it over. He would die for his people. For his Lord. But that wasn’t the question. The pirate didn’t care if he wanted to be imprisoned or not. This was going to happen. So that took out all of the decision making. Or did it? He was sure his Commander would be furious at him if he went back being the prisoner of a pirate instead of the other way around. He was better off if they just killed him now. But, it wasn’t his choice anymore. He nodded.

            “Where to, Captain?” Sam asked with pride in his voice.

            “Tell Kevin to set course for The Playground. Let’s see what ‘childish game’ is in store.” They laughed as Sam walked out of the captain’s quarters. Dean gestured to the man standing behind Jimmy. “Zeppelin, take our guest to his quarters.”

* * *

 

            The Playground is what pirates like to call the Lord’s castle. Why this is, Jimmy couldn’t tell. Must be some kind of joke between pirates. Jimmy didn’t find it all that funny. In his troop, it’s an honor to be able to walk in the castle with permission from the Lord. Because of this Angels call it Heaven. Now _that_ is funny. Get it? Angels. Heaven. It’s funny.

            Jimmy couldn’t tell where they were going. The cell in the lower deck had barely any light. And the light it did have came from the holes in the bars above him. These holes gave no windows to see what was going on so the Angel was forced to be at wonder of what the damn pirates were planning. The cell itself was not pleasant. That was sugar coating it. The wood smelled of salt, barnacles, and dung. The air tasted slightly metallic. He wasn’t sure if that was just the air or if it was from the blood in his mouth. Could be both. His chains bruised the skin on his wrists. Everything in general just ached and bruised. Everything felt wrong. He had cuts all over his face. He may also have had a broken rib, or at least a fractured one. A sudden burst of an idea made his head ache.

            “Hey… Hey!” he called out to the people above deck. He did this for what could have been an hour before someone did finally answer.

            “What the fuck do ya want, Angel?” one of the crew members growled.

            “My ribs… I… I think they’re broken…,” Jimmy grunted through the pain. The man above him wasn’t impressed.

            “Yeah sure buddy.” The man got up to walk away.

            “Wait! Wait! Please! I’ll die if I don’t have medical attention! You don’t want to have a dead Angel on your hands, do you?” Jimmy tried to reason. This made the man stop.

            “You’ll die?” he asked, bending down again. Jimmy tried to look very in pain. Which wasn’t too hard.

            “Yes. Now please, I’m sure you have a doctor on hand,” he persuaded. Then, Jimmy heard another voice.

            “Mr. Bowie! What lovely conversation are you having with the prisoner?” Dean Winchester called over. His steps made the wood above Jimmy creak. This might put a dent in his plans.

            “Apparently he’s hurt, Captin’. Says he’s got broken ribs. He’s been bitchin’ about them for the past hour,” he reported. The pirate captain chuckled. Jimmy saw his face pop out so he could see it.

            “You hurt princess?” he taunted. Jimmy huffed, trying to look a little tougher.

            “I have broken ribs, you bastard. If you bring me to my Commander in this state… you think you’re in war now? Just wait. I am the most respected soldier in the Garrison. I will not stand-.”

            “Ok, ok, jeeze, buttercup. I’ll bring over Alex if you’d just quit whining like a little bitch.” He sighed as he got up. The pirates took their sweet time getting a doctor to him. Another hour passed before someone came down. And it wasn’t quite what he expected. It was a woman he first noticed. Raven hair framed her icy blue eyes. She looked a lot more professional than the rest of the pirates. Her clothing clean and neat, she looked exactly like the doctor that treated Jimmy’s wounds. He guessed it was true that all doctors dressed to impress.

            The woman, Alex, Jimmy remembered, looked to him with a mix of anger, distain, and boredom. He remembered that look at the dock. She immediately got to work. Dean looked over for a few moments watching her begin her work.

            “If he gives you any trouble, knock him out. You can treat him unconscious,” Dean said. Alex gave him a weird expression.

            “Eye, eye, Sir!” she said enthusiastically. Dean rolled his eyes and got up to walk away. Then, they were left alone. Jimmy was starting realize that all members aboard were very skilled at what they did. Combat and all. Still, he had no idea how good a pirate doctor was. He hoped for the best.

            She didn’t talk much to him. She only told him that he had bruised ribs and started to treat them. The silence was overwhelming. Remembering his plan, he tried to strike up conversation.

            “So, you are a doctor,” he started. Wasn’t his strongest line but it got a response.

            “No shit. What about it?” she shot back. In treating his wounds she wasn’t the kindest. He decided to be as nice as possible. She could end his life just as much as save it.

            “It is just unusual I thought. It’s not every day you see a woman in a medical role,” he pointed out. He slightly cringed at the pain of her pressing on his chest.

            “I wonder who’s fault that is,” she wondered, looking at him dead in the eyes. He gulped looking away.

            “Why… uh… Why do this then? Help the pirates. Don’t you want to be free? Are you a prisoner as well?” he asked, placing the bait.

            “Of course you would say that,” she scoffed, tending to his cuts now. She looked to his confused face and seemed to become angrier. “I am perfectly free. I am feed well, paid well, can do whatever I want, and most of all, am respected for my craft. Not because of who I am but because what I do. Ya know, like how everyone should be. When I was under the Lord, I was ridiculed for what I wanted to do. _Especially_ by Angels. Here, I am the most free I’ve ever been. Here, I am respected. So don’t you come here thinking you’re the shit. You’re _not_. You’re _nothing_ ,” she seethed. All Jimmy could do was gawk. What she said was true, he was starting to realize. But, no, the Lord and his rules are good. Aren’t they? If what she said was real, then everything he knew was a lie. But, why would his Commander lie to him? It didn’t make any sense.

            “I would treat you with respect,” he offered to her. He said it because it was true. Looking at her methods she was extremely savvy with medical science. However, he wouldn’t know. But he also said it as a sort of sorry. Sorry you had to go through that. Sorry I didn’t notice. The worse part about it was she looked young. The pain in her eyes made it hard to see anything else. Once again he felt this overwhelming sense of guilt.

            No. _NO_. She was a pirate. Like the rest of them. Why should he be sorry? They kill, and rape, and steal for their own gain. _They_ are the ones who are nothing. Not him. He couldn’t. He… just couldn’t.

            “I would treat you with respect if you weren’t part of such a savage and meaningless cause,” he finished, slightly choking on his words. Her slightly softer expression was then filled with white hot rage. She packed up her things hurriedly and climbed out of the cell, locking him in. He was forced to sit and regret his words. Confusion and anger clouded his mind. He lost all sight of his mission now. He didn’t even remember what it was. He knew it involved the pirate. The pirate, Dean Winchester. Jimmy saw just how invested his was in his crew, his cause, his _family_. He’d only seen snippets but what he could hear, Dean didn’t rule with an iron fist. It was democracy. Everyone had free speech. Free will. All Jimmy had ever known was war and slavery. On this little island of a ship, people were free to be whoever they wanted. This foreign concept messed with his brain. But it wasn’t foreign. He had that once. He had family once. Why didn’t he have it know? Where did it go? A realization cleared his mind. Pirates took it away from him. They took everything he loved. Then, for a moment, Jimmy was at peace. However, it wouldn’t last for long as he heard the boards above him creak loudly and quickly, as if someone was stomping on the deck.

            The barred hatch above him swung open and a man dropped down. This man, then, promptly struck him across the face with a hard blow. Jimmy stumbled back in the small space, falling on his ass as the man repeatedly hit him. Jimmy was too weak to fight back. He put his hands up in either defense or surrender. The blows stopped.

            “Think. Twice. Before. You. Speak,” a gruff voice growled. Jimmy’s vision focused on none other than Dean Winchester above him.

            “What?” he coughed out.

            “I’m starting to want to bring you to your master shish kabobbed on a nice spike. Ya think he’d like that?” He picked Jimmy up by the shirt, making him stand. “I’m just about done with your smart ass. You think you’re so big and tough, huh? Try taking care of 30 men and women on a ship. I _saved_ them. From people like you. Your kind only saves yourselves. We took a vote. _Everyone_ wants me to kill ya. I’m only keeping you alive for whatever money is in store and cause you saved me. That. Is. _It_. So buck up little soldier. The road ahead is not lookin’ too bright for you,” the Hunter barked. He dropped him then climbed out to leave him alone once again. Only this time much, much more bruised. And he had a hunch he wasn’t going to get medical attention this time.

           

**Notes for the Chapter:**

> Hello Readers! Loooong chapter. This was tough to crank out but I kinda like it. Anyway, hope you enjoyed! Till you read again.
> 
>  
> 
> -Alph <3


	4. An Offer I Could Definitely  Refuse

**Summary for the Chapter:**

> A deal has been struck that will determine what side Jimmy chooses. Let's hope he chooses wisely.

Three days. Three days Jimmy spent cold, hungry, and alone in that bird cage. Only one meal a day containing stale bread, some kind of mystery meat, and a small cup of water. The meals came at about mid-day. And for the rest of the day he went hungry. Three painfully painful days he endured the starvation, dehydration, and sleep deprivation. He heard no word from Dean, his brother, or anyone else for that matter. The only one he had to talk to was the musician; Sully. He was very kind and made great conversation. In conversation he would break into song for the soldier to illustrate his point. Jimmy learned a lot from the flamboyant pirate. Everyday his idea of the bloodthirsty savages morphed into misunderstood heroes.

Sully taught him a lot in just three days. And as the days went on, guilt swallowed his heart whole. Since Sully technically wasn’t supposed to talk to him he had to leave after a while. This would leave Jimmy in intermissions of self-loathing, sadness, and confusion. Not only for his situation but the situation of the pirates. With his mission completely forgotten, he somewhat welcomed the idea of Angels and Hunters living in harmony. Not the Demons, however. They were the true evil, Sully had told him. That he could agree with. Even then, he still couldn’t get the bad taste of pirate out of his mouth. Every time he would get close to forgiving them, he pulled himself back with the idea that they were trying to trick him. He still couldn’t trust them. Not fully at least.

On the fourth day everything turned on its head when he was ushered to the captain’s quarters. He was left alone with the captain himself, with Jimmy seated in a chair, hands and feet bound. The Hunter paced back and forth, tossing an apple up and down, not saying a word. Jimmy remembered their last conversation which made his muscles tight. Finally, he stopped and faced the Angel. Jimmy kept his expression as calm and stern as possible.

“Do you know why I brought you here today?” he asked, taking a seat himself. Jimmy stayed silent. “You, just so happen to be a soldier. Being one you would know the ins and outs of the castle and its guards. No?” Silence. “You are going to tell me everything I need to know about the place in order to get in,” he finished taking a large bite of the apple.

“I’d die before I’d betray the crown,” Jimmy growled.

“Thought ya would say that,” Dean sighed. The captain got up from his chair and walked behind the Angel. He suddenly grabbed Jimmy’s shoulders which made him jump. The Lieutenant cringed at his own fear and quickly settled himself. “I’m going to make you a deal,” the pirate whispered in his ear. “You, tell me, what I need to know, and I’ll pretend that you were the one to capture me. No tricks. No gimmicks,” he offered, taking another bite right next to the Angel’s ear. The squishy crunch made Jimmy squirm.  

The offer made him worry. He didn’t know what they were planning. What would happen if he agreed? The pirates could do much damage if he gave up any information.

“What would you gain from this, pirate?” he spat. The Hunter walked out from behind him to look him in the eye.

“That’s none of your concern. But your concern should lie with that little family of yours,” he hummed, a devilish grin carving his face. He wasn’t truly serious. Jimmy chuckled. “What’s so funny, soldier?”

“My family is dead, you idiot. You know who killed them? Pirates. Blood. Thirsty. Pirates. And you wonder why I hate your kind so dearly. They slaughtered my wife _right in front of me_. And burned my _daughter_ who was trapped in the house. She was just _ten_. So, ask me again to help you. No glory, no payment, will ever satisfy me more than when you are caught and hung for your crimes, you skamelar!” he yelled. He felt like his breath was removed from his lungs. His mind spun and tears burned the back of his eyes. Jimmy always became like this talking about his wife and daughter. He would soon regret telling the man about his past, but at the moment he didn’t care. The velocity of his furry and rage could rival that of a storm. However, his anger seemed to have little effect on the pirate. Whatever surprise he did have was quickly concealed by coldness and anger on the Hunter’s face.

“We’ve all lost people. And I would assure you, you lost them to Demons. They are the true enemy here. I lost my mother to them when I was only _four_. They burned every happy thing in my life. After they murdered my father, I was forced to care for my brother and crew all alone,” Dean confessed. Jimmy was stunned at the heart and pain of this pirate. But his hatred continued.

“Then why become the thing you hate? Why fight against us when we can fight together?” he questioned.

“You don’t understand. How could you? You’re one of them. You think the crown is _so_ righteous. When my mother died my father _begged_ for them to help. Ya know what they did? _Nothing_. Fuckin’ nothing! After that we noticed that we weren’t the only ones hurt by the Angel’s greed. _We_ are the ones saving. _You_ just feed off the war and its benefits,” he exasperated. The captain then called in Zeppelin who promptly threw him back into his cell.

* * *

 

            Two days later he was called in again. This time, Jimmy was met with a plate of meat and good bread as well as medical attention. And, unlike the last time, he kept conversation very short with the doctor Alex. At first he was surprised at the treatment. He felt ten times better than he had the entire time he’d been on the retched ship. However, glee quickly turned into suspicion.

            The pirate captain glided in with a pep in his step, as if their last encounter didn’t end the way it did. He stood in front of the soldier with a plastic smile pinching his cheeks.

            “I think we got off on the wrong foot, soldier,” Dean said sweetly. Jimmy didn’t like this. Not one bit. Something was up, he could tell. “You are weary, I’m sure. Our last conversations have been… less than pleasant. However, I think we have something to gain from each other,” he explained, the last words turning his lips into a grin.

            “What do I have to gain from a pirate?” Jimmy dead-panned. Cocky? Maybe. However he didn’t want to let his guard down again. Since their last interaction Jimmy has felt exposed. He said way too much to the Hunter, and in turn, has heard too much. That night they poured their souls to one another hoping something would stick. He was just too terribly confused. Everything he had ever believed was a lie, or at least a prejudice. But they had to be the ones lying, right?

            As the days went on Jimmy grew tired from playing that game. _Who was lying?_ He couldn’t tell to save his life. All the Angel wanted to do was go home. To his hole in the wall. To where everything made sense. To where he was right. He was just done with this nightmare. He hated pirates, he hated this ship, he hated Angels, and most of all he hated himself. He was just _done_.

            Pulling himself from his thoughts, he heard the drained pirate sigh.

            “I… I’m sorry about… your… uh… family,” the Hunter apologized, dropping his act. This made Jimmy straighten in his seat.

            “Condolences to your family as well,” he echoed, confused.

            “I don’t need your pity, I just need your help.” The pirate steadied himself. “If you tell me where the cells are and where I can find a key for ‘em, I’ll let you turn me in. No strings attached,” he explained.

            “Why do you need to know that?” Jimmy asked.

            “None of your fuckin’ business. The point is I need to get someone out who was wrongfully accused. After that, I’ll do whatever you bastards want me to do. For a price,” he brushed off.

            “I must tell you, if it is any friend of yours, they may already be dead. It is by law that pirates must be hung immediately, for their crimes,” the Angel warned. Mostly he was staling, but what he said held nothing but truth.

            “She’s not a fuckin’ pirate! She’s innocent and it’s all my fault,” he said harshly. Jimmy slightly pulled back. Dean did the same as he took in a long breath. “Just tell me. Ya don’t really have an option here,” he concluded. Jimmy stayed silent for a moment, then answered.

            “I need to be promised something in return if I am going to be giving up information.” The Hunter looked to the soldier with glower, not being slightly amused.

            “Seriously? You get all the glory points for ‘capturing’ me. What more could you want?” Dean demanded, gripping to the sides of the chair Jimmy was sitting in.

            “If I am to bring you to my Commander, you are to gleefully accept whatever offer they give you. Payment and all,” Jimmy insisted. The pirate scoffed and moved to be behind his desk, and sat in his chair. “No ‘glory’ would come to me if you resisted,” he added with authority. Another scoff. “I will not tell you what you want if you don’t promise, and uphold your promise,” the Angel concluded, crossing his arms. The captain suspired, facing Jimmy with distain chiseled into his features.

            “Fine, sure. Whatever,” he decided. He wasn’t satisfied with the answer.

            “Do you promise, Dean?” he inquired with seriousness. The name felt foreign on his tongue, tumbling in his mouth before vibrating his lips and into the air. He had barely called the pirate by his name since he has known him, Jimmy noticed. The pirate seemed to notice as well and his stone expression melted ever so slightly.  

            “If it’ll get ya to cough up the details, I promise.” The Hunter got up again and got threateningly close to the soldier’s face. “Mark my words, bird-brain. If things go south, Ima get me and my crew outta there. And that, is a promise,” he finished, leaning on his desk. “Well… tell me.”

            “Tell you what?” Jimmy asked.

            “Tell me what I need to know.” Hesitantly, Jimmy did give up the information about the cells and how to open them. However, he did omit some crucial details. These details would give him the upper hand in capturing his whole crew, and ridding the world of “The Demon Hunters”. He may sympathize with them, but that still leaves years of treachery from them. What they’ve done is inexcusable. Jimmy will bring them to justice, for the good of the Lord. And _that_ , is a promise.  

**Notes for the Chapter:**

> Hello Readers! This took a long time for not a lot of words. Oh well! Trying to get the plot straightened out before I continue. Might take a longer while before next update. Hope you enjoyed! Till you read again.
> 
> -Alph <3


	5. Crack in the Glass

            A comforting warmth burned his throat as he downed his third beer. A similar flame danced on the candle wick, illuminating the room as the boat swayed. The dull smell of gunpowder mixed with the sharpness of the sea salt stung his eyes with nostalgia. Bitter the memory was for him. He had no other choice. His brother- the only good thing he has in his life- was going to die and he could not let that happen. He basically traded his soul for Sammy. They took him away to Lucifer, and the son of a bitch tortured his ass to hell and back. He still had nightmares; there wasn’t enough beers or whiskey to swallow that pain. He had no regrets, however. No matter the horror, no matter the danger, he would do anything for his brother. But this wasn’t the reason why he was up past midnight. Not that being in hell never escaped his mind. That would never leave him.

            No, Captain Dean Winchester had another demon nagging at him that night. The Lieutenant Jimmy Novak. He just couldn’t figure him out. What did that son of a bitch want? One moment he was god-crazy soldier, the next, he was a sad ass bastard begging to be understood. This fact made the Hunter hate the Angel more. Although, he couldn’t help but remember the desperation and anger in his eyes, talking about his gal and kid. Sure, Dean felt bad about that but, it wasn’t his fault. It wasn’t his fault that the army is incompetent. It wasn’t his fault that he has to do what needs to be done to survive. If anything, it’s Mr. Soldier’s fault. He only drags out his and other’s pain by staying with the crown. They’ve all lost people, it’s not an excuse to murder others for your own selfish gain.

            A knock was heard at the door. Dean hummed loud enough for anyone outside to hear. The door creaked open. He quickly hid the two empty beer glasses under his desk. A tall man with a tuff of brown hair walked in.

            “Heya, Sammy. What brings ya here?” Dean greeted his younger brother.

            “You should be asleep, brother,” Sam huffed as he sat down in front of Dean.

            “Could say the same for you, brother,” he responded leaning back in his seat. Sam gave him a look that he promptly ignored.

            “Somethin’s on your mind. What is it?” he inquired. Dean passed the bottle between his hands, nervous. He could almost laugh. Samuel Winchester; straight to the point. Dean could see that being captain really solidified the man’s confidence and changed his attitude about somethings. Sam became more of a man without him than with. That made Dean feel like absolute crap. So, to cover up pain; jokes.

            “Just thinking about how much that mop on your head needs a trim,” he jested, chuckling slightly.

            “It’s the Angel, isn’t it?” Crap. The Captain’s brother could see through his shit like a window. Dean should know better than to lie to Sam, from experience it’s only brought heart ache. He sighed.

            “Sam, I just don’t know what to do with him. One minuet he’s a brain-washed soldier, and the next, a sad bastard with a dead wife and daughter,” he confessed.

            “Maybe he’s just as confused as you are,” Sam offered. Dean huffed. “Didn’t you get the info you wanted? After we invade the Playground, we won’t ever have to deal with em’ ever again. Right?” The Captain shrugged and turned away from his brother.

            “He gave me the ins and outs of the dungeon. Once I give myself up, you and the crew go down there and get them. If I don’t come back, tell her I’m sorry,” Dean reported. The younger brother chuckled. He asked Sam what was so funny.

            “Even after all this time, you still care about Lisa,” Sam explained. “Ben too.”

            “Yeah? What about it?” Dean gritted, turning to face Sam.

            “It’s just unlike you is all,” he shrugged.

            “Shut up.” Sam chuckled again and got up to leave. He wished his older brother a good night and Dean did the same. As the door clicked shut Dean let go of a breath he didn’t know he was holding. What the future held he had no fucking clue. All he knew was that he was going to get his Lisa and Ben out of that cell, and maybe get some money along the way. It was his fault that they were in there in the first place. It was his job to get them out.

            Dean looked to the empty bottles on the floor and in his hand. One more wouldn’t hurt.

**Notes for the Chapter:**

> Things are about to get messy. Hope you enjoyed! Till you read again.
> 
> -Alph <3


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